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A peaceful Hamptons neighborhood nestled on the North Fork of eastern Long Island, the exquisite Southold hamlet invites residents to enjoy wide-open farmland and small-town charms from antique shops to roadside produce stands. Established in 1640 as New York’s oldest English settlement, Southold continues to evolve today.

Dotted with acres of open farmland, world-renowned vineyards, and ample space devoted to public parks, the delightful community with a rich heritage continues to thrive with unique shopping opportunities, top casual and fine dining fare, historic buildings, beautiful museums, and unlimited recreational opportunities.

Its countrified qualities, culture, and history make Southold a special place to live, especially for those who prefer homes set on well-tended acres of farmland rather than tracts best measured by the square foot. Southold is a nirvana for residents who prefer natural island beauty over suburban life or summer hotspot festivities.

The hamlet of Cutchogue is home to not just Long Island’s first winery (established in 1973) but also one of best surviving examples of domestic English architecture in the United States. Peconic—named for Peconic Bay and once home to Albert Einstein—has roots as a noted artists’ haven dating back to the early 20th century.

Walk the unspoiled beaches along the Long Island Sound and Noyack Bay, rich with stretches of pristine sand. Known for its wine culture, Southold’s North Fork features sprawling vineyards and wineries open year-round for tours and tastings. Also part of the township are Robins Island, Plum Island, and Fisher’s Island.

Contact Team Rita today to schedule viewings for homes in Southold, New York. Call to schedule a free consultation with one of our real estate agents.


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  1. 4 Beds,  3.5 Baths
    3,000 sqft   lot 1.06 ac
    MLS 842796
    1 Days on Market
  2. 5 Beds,  2.5 Baths
    2,726 sqft   lot 1.09 ac
    MLS 843095
    1 Days on Market
  3. 3 Beds,  2 Baths
    1,575 sqft   lot 28,314 sqft
    MLS 842408
    1 Days on Market
  4. 4 Beds,  2 Baths
    1,911 sqft   lot 30,492 sqft
    MLS 842341
    1 Days on Market
  5. 4 Beds,  3.5 Baths
    3,300 sqft   lot 1.25 ac
    MLS 842464
    1 Days on Market
  6. 4 Beds,  5.5 Baths
    3,000 sqft   lot 25,265 sqft
    MLS 806509
    2 Days on Market
  7. 3 Beds,  2 Baths
    1,650 sqft   lot 40,076 sqft
    MLS 841740
    5 Days on Market
  8. 3 Beds,  2.5 Baths
    1,500 sqft   lot 14,375 sqft
    MLS 839291
    6 Days on Market
  9. 3 Beds,  2 Baths
    1,348 sqft   lot 1.09 ac
    MLS 840964
    6 Days on Market
  10. 5 Beds,  3 Baths
    2,300 sqft   lot 13,504 sqft
    MLS 840724
    7 Days on Market
  11. 2 Beds,  2 Baths
    730 sqft  
    MLS 839103
    8 Days on Market
  12. 4 Beds,  3.5 Baths
    4,400 sqft   lot 43,560 sqft
    MLS 840028
    8 Days on Market
  13. 4 Beds,  5 Baths
    3,000 sqft   lot 4.18 ac
    MLS 835584
    9 Days on Market
  14. 4 Beds,  4 Baths
    3,400 sqft   lot 17,424 sqft
    MLS 835289
    10 Days on Market
  15. 2 Beds,  1 Bath
    965 sqft   lot 6,970 sqft
    MLS 838917
    11 Days on Market
  16. 3 Beds,  1 Bath
    1,200 sqft   lot 14,811 sqft
    MLS 839087
    13 Days on Market
  17. 4 Beds,  4 Baths
    3,000 sqft   lot 3.34 ac
    MLS 836156
    13 Days on Market
  18. 3 Beds,  4 Baths
    2,455 sqft   lot 12,633 sqft
    MLS 830474
    13 Days on Market
  19. 4 Beds,  2.5 Baths
    3,800 sqft   lot 37,026 sqft
    MLS 837853
    14 Days on Market
  20. 3 Beds,  2.5 Baths
    2,300 sqft   lot 23,087 sqft
    MLS 836867
    15 Days on Market
  21. 3 Beds,  2 Baths
    1,500 sqft   lot 17,860 sqft
    MLS 836097
    16 Days on Market
  22. 2 Beds,  1 Bath
    805 sqft  
    MLS 836263
    16 Days on Market
  23. 2 Beds,  2 Baths
    1,350 sqft   lot 9,148 sqft
    MLS 836106
    17 Days on Market
  24. 3 Beds,  2 Baths
    2,000 sqft   lot 35,284 sqft
    MLS 836065
    17 Days on Market
  25. 4 Beds,  3 Baths
    2,310 sqft   lot 9,148 sqft
    MLS 821439
    18 Days on Market
  26. 2 Beds,  2.5 Baths
    1,800 sqft   lot 732 sqft
    MLS 835501
    19 Days on Market
  27. 3 Beds,  1 Bath
    1,205 sqft   lot 10,019 sqft
    MLS 835632
    19 Days on Market
  28. 3 Beds,  2 Baths
    1,535 sqft   lot 40,076 sqft
    MLS 833997
    20 Days on Market
  29. 3 Beds,  1.5 Baths
    1,565 sqft   lot 1.60 ac
    MLS 824693
    20 Days on Market
  30. 3 Beds,  1 Bath
    1,300 sqft   lot 13,940 sqft
    MLS 835064
    20 Days on Market
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